In the opener, Martinique faces Trinidad & Tobago, immediately followed by an encounter between Haiti and Cuba.
Each of the four sides took distinctly different routes to the final four in keenly contested tournament that has had its fair share of surprises; none more astonishing than the elimination of two-time defending champion Jamaica.
On the last day of Group A play, eight-time champion Trinidad & Tobago needed to beat the Dominican Republic and hope that Haiti defeated host Antigua and Barbuda. Much to the Soca Warriors good fortune, that is exactly what occurred.
Trinidad narrowly edged the Dominicans, 2-1, and, then, Haiti nipped the Benna Boys 1-0. The result meant that Trinidad would advance in the competition, plus qualify for the Gold Cup for the first time since 2007.
Team captain Jan Michael Williams believes that his team has found its groove at the right time.
"We have seen all three of their (Martinique) games, we come into this game very confident but we also give Martinique the respect they deserve because they topped a group with the likes of Jamaica and Cuba," said the goalkeeper. "We are not taking them lightly, they are a very tactically team but we are ready."
Admitting that his team has not played to its full potential so far in the tournament, Williams was secure in saying that the fans will see a more organized Trinidad in the knockout rounds.
"We have had a lot of issues in the past leading up the tournament, but the confidence is there and we hope to fully gel on Friday," added the 28-year-old, who plays with DirecTV W Connection. "Our main objective was to qualify for the Gold Cup and if winning the CFU title happens, it will be a plus for us."
Martinique, which won the 1993 Caribbean Cup, has appeared in three previous Gold Cups, advancing to the quarterfinals in 2003.
Patrick Cavelan, the Martinique head coach, told CONCACAF.com that the game against Trinidad will be difficult, but he believes that his team can advance to the finals; especially with the outstanding Kevin Parsemain at the ready.
"He is a very important player, who can score anytime and draws attention to him that allows other players to get involved which makes us dangerous," stated Cavelan in praise of striker. "We are very happy because for the past ten years we have not played in the Gold Cup and we really wanted to qualify."
Parsemain, 24, has netted once at the Caribbean finals, but has scored 12 goals in nine games overall in the competition this year.
Haiti won its only Caribbean Cup in 2007, while Cuba -- its semifinal opponent -- is looking for its first title. An interesting twist to their meeting is that the Haitians are coached by Antonio Blake, a Cuban by descent.
"I never coached against them before, but yes it would be nice to defeat them," said a smiling Blake. "Haiti is a good team and we are happy to be in the Gold Cup.
"Our players are strong and fit and we want to win everything. The last competition we played in we weren't able to qualify for the Gold Cup and it disappointed us."
After an opening 1-0 loss against Martinique, Cuba showed improvement in winning its next two games and qualifying for a sixth Gold Cup.
"We have achieved one of our goals so far (Gold Cup) now we have to finish by winning the competition," said Cuban head coach Walter Benitez. "Our style of playing is a flowing football where we create chances for our strikers and trust each other.
"Haiti is a good team, but we are ready and will give of our best."
The stage is set for an enthralling round of semifinal matches.